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Highly Asymmetric NHC-Catalyzed Hydroacylation of Unactivated Alkenes


  • We are grateful to Karin Gottschalk for skillful technical assistance. Generous financial support by the Deutsche Forschungsgemeinschaft (SPP 1179 and SFB 858), the Fonds der Chemischen Industrie, AstraZeneca, the International NRW Graduate School of Chemistry (I.P.), and the Deutsche Akademische Austauschdienst (K.H.) is gratefully acknowledged. The research of F.G. was supported by the Alfried Krupp Prize for Young University Teachers of the Alfried Krupp von Bohlen und Halbach Foundation. NHC=N-Heterocyclic carbene.


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NHC-catalysis proto(n)type: The title reaction produces 21 different chroman-4-one-type products in good yields and excellent enantioselectivities, in each case building up a new all-carbon quaternary stereocenter (see scheme). Based on DFT calculations a mechanistic scenario involving proton transfer, possible transition states, and a mode of enantioinduction is presented.